Holiday rentals with outdoor seating in Chesterton

Bright Modern Designer Maple Street Beach House

Beautiful renovated house on wooded lot, half mile to the Warren Dunes! Home completely designed for the ultimate vacation rental getaway! SS kitchen, memory foam mattresses, marble bathrooms w/walk-in shower on main floor & full bath w/tub up, hardwood floors, gas fireplace in sitting area and great room that connects the living/dining and kitchen. Roast s’mores, grill steaks & sip local brews in the private backyard w/ fire pit. Central to everything in Harbor Country. Come enjoy winter w/us!

Cozy warm Glamping escape

Blooming Bus farms is an urban regenerative micro farm producing free range eggs from our happy chickens, Alpaca fiber & compost from our herd of 5, and U-pick flowers in the summerl Explore our 15 acres via trails throughout, and play some games on our sand volleyball court, or shoot hoops farm style! Established in 2021, we are still completing our vision which includes 4 Glamping sites, event space, a food forest, mushroom cultivation, vermicompost, and the restoration of a 1947 Fitzjohn Bus.

New Buffalo retreat - Perfect year-round getaway!

Located in the heart of New Buffalo and walking distance to everything, this recently remodeled cottage is the perfect place for an escape. With an open kitchen/porch concept, leading out to a massive natural wood deck, your entry to a huge fenced in corner lot, there is no shortage of space for any summer activity or just to get back to a quieter, more relaxing pace. In winter months New Buffalo is just as charming with fewer visitors and plenty of opportunities to explore the area. CR23-0048

The Lucky Charm House -Walk to it all! Cute, cute

Cute as can be, super comfy, 3 blocks to downtown 3 Oaks. Walk to Acorn Theatre, Journeyman & shopping in an eclectic quintessential small town 90 mins from Chgo. Hike local trails, beach it up at Warren Dunes State Pk, bike ride country roads -Explore Harbor Country. Wonderful dining, brew pubs and wineries to explore. Open living space w/large DR. Primary BR +bth w/shower. 2nd BR w/full bed +single bunk. Large back porch +fenced yard. 2 large TV’s, Wifi/cable. Daybed front porch.

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Location! Location! Location! Prime Wicker Park Location on Milwaukee! This spacious, cool, vibrant, eclectic, fully equipped apartment is close to everything, making it easy to plan your visit. Bright top floor unit with a private patio to just chill and unwind or walk downstairs and your literally in the heart of Wicker Park. Super easy access to downtown nightlife/lake/museum all within 15 minutes and super easy commute to O'hare. CTA busses all around and a 2 minute walk to the Blue Line.

Escape to The Sunshine Cottage of Harbor Country!

Cozy up at The Sunshine Cottage of Harbor Country. Surrounded by award-winning beaches, state parks, wineries, and breweries this location boasts endless activities within a short walk, bike, and drive. With a large backyard and extended porch deck, the cottage offers outdoor fun and entertaining all summer long, or retreat for a cozy winter getaway. The cottage is in close proximity to Lake Michigan and Grand Mere State park - sand dunes, hiking trails, and nature adventures all seasons.

Relaxing Glamping Experience in a Tiny Cabin

Experience a serene and relaxing getaway in our off-grid tiny cabin on our farm. Created with the intention of slowing down (no tv, no wifi and no refrigerator), enjoy wandering the fields relaxing in one of the hammocks, cooking on the outdoor fire pit, sipping coffee on the front deck and generally taking a break from modern life. If you'd like to explore the area, we are nearby popular trails and bike routes, U-pick farms, breweries & restaurants and beaches along Lake Michigan.

Superhost, hot tub, golf cart, fire pit, large!

Newly renovated 5 bed, 2 bath home in the quaint village of Grand Beach. Golf cart included with rental (in season - May thru mid-Nov). Home is situated on a large lot, high on a sand dune that overlooks the 6th fairway and park area. Enjoy two large decks and year-round eight person hot tub. The property is very private, on secluded street and fully stocked for a great stay. It's a great place to enjoy some down time in an idyllic village in the heart of Michigan's "Harbor Country."

Walk to ND/Eddy Street, ProCleaned/Comfy/Updated

Stay in a newly remodeled home within easy walking distance of the Notre Dame campus and the Eddy Street Commons dining and shopping district. Designed exclusively to be enjoyed by short term renters. I strive to give you the amenities of a fine hotel but with the space and privacy of home. As an experienced host with perfect reviews, I pride myself on providing the comfort, cleanliness, and lots of extra touches to make your stay comfortable and hassle free.